It is not just a question of whether you have driven in snow. It is that some of these hilltowns are incredibly steep and walking in them in winter if it is icy or snowy is next to impossible. The natives wait it out but if you are traveling it creates pressure.

I could be wrong but I think even the most devoted Gubbio lover would not stay there for an entire week in January and possibly not even in spring. I would suggest seeing Gubbio from Perugia as a day trip and spend that 3rd week in Arezzo (and see Cortona from there as a day trip.)

cafegoddess - you may want to start another thread I'm getting confused between your plans and MariaG's! That said, having a long time to spend is simple grand. Our month in Italy was so wonderful, but I also would have loved just having those two weeks in Umbria, if that had been our entire vacation.

If your travels take you anywhere near Monte Castello di Vibio (about 30 km south of Perugia, I can highly recommend a stop at Teatro della Concordia. It is the smallest theatre all'italiana in the world. If there is not a concert, they will let you enter and walk around, if you become a Friend of the Theater, which I think cost a couple of euros. It is totally charming and such a treasure in the tiny town - one of the things I love to discover when in Italy!

http://www.teatropiccolo.it/

Leely - yes, we've stayed in Orvieto for periods before, always loved it. My father came from nearby Bolsena, which I dearly love, but Orvieto has much more to offer for an extended stay. Yes, driving & parking up top is challenging, but we've managed nicely. We have taken day trips from Orvieto all around Lago di Bolsena, to Saturnia, Sovana, Montepulciano, Bagnoreggio, etc., no problems.

Sandralist - yes, we've been to the Parco dei Mostri in Bomarzo - love it!